As we approached the half-year mark, I recognized that I needed to regroup with my internal stakeholders to make adjustments around what we would be delivering for the second half of the year.
You could argue that the half-way point through a calendar year is a somewhat arbitrary juncture, but nevertheless it provided me with a good checkpoint opportunity. Since the beginning of the year, my team had planned, built, tested and delivered product updates through several releases. Before we commenced with the next cycle, I wanted to revisit our priorities and review any significant changes in the business that would require some course correction in the product roadmap.
What drove this decision
I was confident that the Product team had been addressing the full range of demands and that we would continue to balance stakeholders' priorities as we were all committed to satisfying our end customers' needs.
We had already begun to carve out big plans for the next 6-9 months and some of them would require significant investment. I knew we were aligned with individual departments but over time, the various department heads had lost sight of what was most urgent for their peers. It would be more difficult for me to deliver and promote an updated product roadmap without some preliminary group consensus at the topmost level.
The decision: Organize and facilitate a product strategy summit with all the department leaders to revisit and rebalance priorities.
I will be the first to admit that the word "summit" sounds a bit lofty (pun intended) but I assure you this was not some trumped up, off site boondoggle - I'm saving that for my big end of year 1st Annual Product Strategy Retreat.
My goal was simply to get all the department VPs and some key Directors in the same room and run through a formal, Product-focused agenda. I wanted to use the time to review the roadmap choices we had made over the last 6 months (some good, some bad) and continue to push the company to pursue sound product investment decisions.
Balancing 3 related concerns: curb appeal, interior living space, and structural foundation
In the many discussions I had been having with the different departments leading up to this summit, it became increasingly clear that there was a lack of mutual appreciation, if not basic understanding of what was driving the other departments' priorities. A number of the stakeholders were out of touch.
I wanted to share this insight with the invitees but in a way that didn't offend or alienate a particular group. In the summit invite, I offered the following apartment building metaphor to help explain the different, but complementary perspectives of each group:
- Sales wants the building to have massive curb appeal, to look good from the outside so as to increase the chances of attracting new customers.
- Customer Success wants all our new tenants to have a smooth move-in experience and to enjoy living in their new home for many years.
- Operations wants to make sure the building itself can safely support all the tenants and their various housing needs.
And of course everyone in the organization should be focused on increasing customer satisfaction as it will lead to renewals and referrals!
Plan of attack
Setting proper expectations: everybody wins! everyone loses!
I started the meeting by setting expectations for the group - which largely meant telling them that no one was going to get everything they wanted. The summit was an exercise rooted in compromise. I told them that it was equally important for them to defend their own priorities as it was to become more aware of what the other departments were struggling with.
The bulk of our time in the summit was spent prioritizing a lengthy list of wish list items. To kick things off, though, I offered an assessment of the past six months to remind everyone why we built the things we did and to get some feedback.
Review the roadmap themes for the year
I first presented the product strategy I had introduced at the beginning of the year that outlined how I would be making decisions for the next 12 months. Specifically, I highlighted the roadmap themes that were established back then and verified with the group that we were still confident in those decision-making guidelines.
Review 1st six months
Building on the initial validation from the group, I proceeded to show how the recent product decisions we had made were in line with the roadmap themes. This brief, high level review of the advancements we had made in our product portfolio over the past 6 months provided an ideal opportunity to explore queries such as:
- How accurate was the original plan and how close did we come to hitting our targets/metrics?
- Are the major initiatives still on track or have there been new insights that require us to adjust our course?
- What have we learned about estimating work, about dependencies, about our ability to accurately respond to customer demand?
I was certainly pleased to hear the group confirm that the first half of the year was largely productive and that we had been made solid product investment decisions.
First pass at prioritization
From the Trello board I created to capture individual wish lists for the different departments, I pulled the top 30-40 cards to start the prioritization exercise. The first step was to bucket the items into either one of only two lists: High Priority or Low Priority.
This first pass proved to be relatively easy for the group. I was pleased to see the Low Priority list ultimately accumulate many more cards which meant the final pass would be that much easier.
Overall, it was a constructive discussion. None of the participants were particularly unreasonable and did not fight excessively for their own items. I did occasionally use the following prompt when we seemed to be getting stuck: "Can we get through the second half of the year without spending any time on this item?" That was often the only nudging that was required to properly bucket the topic.
Crash course on product constraints
I had prepared a break in the summit schedule in case we needed a cooling off period - and intentionally scheduled the catered lunch to arrive during the break. It turned out there hadn't been that much contention so I instead used the break to revisit some of our constraints and to remind the group about why the next half of the exercise was going to be frustrating for all. Specifically, I talked briefly about the following topics:
- Our true development capacity - what we should really expect from the current size and skill level of our Engineering teams. Read more about setting expectations around Engineering capacity here.
- Software's total cost of ownership - how each line of code we add requires more of our company's resources from Product, Engineering and QA all the way through documentation, support, and training.
- Opportunity costs - each time we agree to start building something new, we must recognize how that will limit our ability to respond to the next "must have" requirement (yeah Sales, I'm talking to you!)
I can't be sure if all the messages landed on point with the entire group but it was my meeting and I was going to take advantage of this ideal product soapbox opportunity.
Final pass at prioritization
In the home stretch, the group now turned its attention to reviewing the much shorter High Priority list (14 items, down from 40). One by one, I went around the table to get individual input. I guided the group by having each of them select 1 primary item and 1-2 backup items.
When we had finished the final pass, we had arrived at a prioritization list that had mutual support from all departments. And I had a clear indication of how I would be adjusting the Product Roadmap for the second half of the year.
Not only did we finish the full exercise (on time no less) with a shared prioritization list but I was told afterwards by the group members that it was one of the more amicable and productive meetings around product direction in which they had participated in recent memory.
I made it clear to the group that the summit was not designed to immediately produce a new or updated roadmap. It would take me more time to work through the items on the High Priority list and factor everything into the Product Roadmap for the second half of the year. Still, I would like to believe the outcome of the summit extended beyond achieving consensus around particular product priorities. I think it represented a milestone for advancing inter-departmental agreement. Maybe next time, I'll refer to it as a Product Peace Accord.